Methanol → Methyl [2-methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)-5-oxazolyl]carboxylate

HRID 350735Notes

Reaction equation

HRID 350735 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:17]([OH:19])=[O:18])=[C:5]([C:7]2[CH:16]=[CH:15][C:14]3[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=3[CH:8]=2)[N:6]=1.S(=O)(=O)(O)O.[CH3:25]O>>[CH3:1][C:2]1[O:3][C:4]([C:17]([O:19][CH3:25])=[O:18])=[C:5]([C:7]2[CH:16]=[CH:15][C:14]3[CH2:13][CH2:12][CH2:11][CH2:10][C:9]=3[CH:8]=2)[N:6]=1

Participants

4

Reactant 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 21088470[2-Methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)-5-oxazolyl)carboxylic acid

Product 1

HCID 23061895Methyl [2-methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)-5-oxazolyl]carboxylateYield 76%

Procedure

To a solution of [2-methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)-5-oxazolyl]carboxylic acid (6.0 g) in methanol (120 mL) was added conc. sulfuric acid (6.0 mL) and the mixture was stirred with heating under reflux for 18 hrs. The reaction mixture was concentrated and the residue was diluted with water. The mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate, water and saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give methyl [2-methyl-4-(5,6,7,8-tetrahydronaphthalen-2-yl)-5-oxazolyl]carboxylate (4.75 g, yield 76%) as crystals. Recrystallization from ethanol gave colorless crystals. melting point: 96–97° C.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 18 hrs
  3. concentrationThe reaction mixture was concentrated
  4. additionthe residue was diluted with water
  5. extractionThe mixture was extracted with ethyl acetate
  6. washThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate, water and saturated brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-d06d760c1be54df8b2551c07c3c2ba02
Source dataset
uspto-grants-2007_02
Patent number
US07183276B2

Reaction notes

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